Water → 4-((1S)-1-{[5-Cyano-2-(3-fluorophenoxy)benzoyl]amino}ethyl)benzoic acid

HRID 1293321Notes

Reaction equation

HRID 1293321 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[C:7]([CH:23]=1)[C:8]([NH:10][C@H:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=1)[CH3:12])=[O:9])#[N:2].B(Br)(Br)Br.O>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[C:7]([CH:23]=1)[C:8]([NH:10][C@H:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)[CH3:12])=[O:9])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 69419342Methyl 4-((1S)-1-{[5-cyano-2-(3-fluorophenoxy)benzoyl]amino}ethyl)benzoate

Product 1

HCID 694173964-((1S)-1-{[5-Cyano-2-(3-fluorophenoxy)benzoyl]amino}ethyl)benzoic acidYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-((1S)-1-{[5-cyano-2-(3-fluorophenoxy)benzoyl]amino}ethyl)benzoate (step 2, 200 mg, 0.47 mmol) in dichloromethane (10 mL) was added a solution of boron tribromide (1 M in dichloromethane, 0.95 mL, 0.95 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature for 6 h. The reaction mixture was poured into water (10 mL) and the whole was extracted with ethyl acetate (50 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (1/1) to afford 62 mg (33%) of the title compound as white solids: 1H-NMR (DMSO-d6) δ 12.86 (1H, br.s), 8.95 (1H, d, J=7.9 Hz), 8.04 (1H, d, J=2.2 Hz), 7.90 (1H, dd, J=8.6, 2.2 Hz), 7.81 (2H, d, J=8.3 Hz), 7.51–7.40 (3H, m), 7.12–6.90 (4H, m), 5.07 (1H, m), 1.37 (3H, d, J=6.9 Hz); MS (ESI) m/z 405 (M+H)+, 403 (M−H)−.

Workup

  1. extractionthe whole was extracted with ethyl acetate (50 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified
  5. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-0c759ad559d946cc868e4e672699c0af
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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